The Grittiest Conversations of 2025: AI, Business & Beyond
In this recap episode, we highlight the best moments from our 2025 interviews and reflect on the ideas that defined the year.
Featuring:
David Rubenstein (co-founder of Carlyle)
Yamini Rangan (CEO of HubSpot)
Ben Chestnut (co-founder of Mailchimp)
Winston Weinberg (co-founder and CEO of Harvey)
Garrett Lord (co-founder of Handshake)
Aidan Gomez (co-founder and CEO of Cohere)
Michelle Zatlyn (co-founder of Cloudflare)
Evan Spiegel (co-founder and CEO of Snap)
Connect with Joubin
X: https://x.com/Joubinmir
LinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/
Email: grit@kleinerperkins.com
Follow on LinkedIn:
https://www.linkedin.com/company/kpgrit
Follow on X:
https://x.com/KPGrit
Learn more about Kleiner Perkins: https://www.kleinerperkins.com/
Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO)
Garrett Lord is co-founder and CEO of Handshake, which started as a career network for college students and new grads but recently discovered something extraordinary: they were sitting on the world’s largest network of academic experts—exactly what frontier AI labs desperately needed. With 500,000 PhDs and 3 million advanced degree holders creating training data, in just eight months they’ve built a new business that hit $50 million in revenue in its first four months and is on track to blow past $100M in the first 12 months.
What you’ll learn:
1. How Handshake found an opportunity to leverage their proprietary network of experts to launch a data-labeling business that’s on track to blow past $100 million ARR in 12 months
2. Why AI models need human experts (e.g. physics PhDs) to improve, and what this “data labeling” actually involves
3. Inside the actual work: what a biology PhD does for 8 hours that makes GPT-5 smarter
4. The playbook for building a startup inside a startup: separate teams, separate offices, separate everything
5. Why the shift from “generalist” to “expert” data labeling created a once-in-a-lifetime business opportunity
6. Why AI won’t eliminate entry-level jobs—it’s creating “Iron Man suits” that make junior employees 10x more productive
—
Brought to you by:
CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny
Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/
Claude.ai—The AI for problem solvers and enterprise: http://claude.ai/
—
Transcript: https://www.lennysnewsletter.com/p/inside-handshake-garrett-lord
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/171410958/my-biggest-takeaways-from-this-conversation
—
Where to find Garrett Lord:
• X: https://x.com/garrettlord
• LinkedIn: https://www.linkedin.com/in/garrettlord/
• Email: Garrett@joinhandshake.com
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Garrett Lord
(05:00) Understanding data labeling and its importance
(13:08) The role of experts in AI model training
(15:35) The future of AI and human collaboration
(24:17) Why AI won’t eliminate entry-level jobs
(27:58) The continuous improvement of AI models
(33:05) The emergence of Handshake’s new business model
(37:07) Incubating new ideas in established companies
(40:42) Handshake's competitive advantage
(45:43) Scaling up and meeting market demand
(48:38) Overcoming challenges and adapting
(53:08) The importance of separate teams and ownership
(57:26) The future of job matching with AI
(01:00:30) The biggest bottlenecks to advancing models further
(01:02:37) Lightning round and final thoughts
—
Referenced:
• GPQA: https://github.com/idavidrein/gpqa
• Handshake: https://joinhandshake.com/
• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai
• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons
• Goldman Sachs: https://www.goldmansachs.com/
• General Motors: https://www.gm.com/
• Google: https://about.google/
• Sahil Bhaiwala on LinkedIn: https://www.linkedin.com/in/sahil-bhaiwala-459b0354/
• Francisco “Paco” Guzman on LinkedIn: https://www.linkedin.com/in/guzmanhe/
• Avery Yip on LinkedIn: https://www.linkedin.com/in/averyyip/
• Game of Thrones on HBO: https://www.hbomax.com/shows/game-of-thrones/4f6b4985-2dc9-4ab6-ac79-d60f0860b0ac
• SNOO: https://www.happiestbaby.com/products/snoo-smart-bassinet
• Careers at Handshake: https://joinhandshake.com/careers/
—
Recommended books:
• Zero to One: Notes on Startups, or How to Build the Future: https://www.amazon.com/Zero-One-Notes-Startups-Future/dp/0804139296
• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
Lenny may be an investor in the companies discussed.
To hear more, visit www.lennysnewsletter.com
Sleeping in Parking Lots to $250M+ Revenue: How Handshake Built Gen Z's Career Platform, Inside its Fast Growing AI Data Labeling Business, Scaling a Three-Sided Marketplace, How AI Changes Hiring
Garrett Lord is the Co-founder and CEO of Handshake, the career and social network for Gen Z, connecting a million employers, 1,600 universities, and 18 million students and alumni.
We talk through the explosive growth in Handshake’s human AI data labeling business, how AI is changing the job market and careers, advice for scaling a three-sided marketplace, and Garrett’s approach to hiring executive-level talent.
We also get into the early days of Handshake, tapping out his dad’s retirement account to fund the first years, driving across the US landing the first customers, sleeping in McDonald’s parking lots, sneaking into careers fairs, and inside Handshake’s first fundraise that took over seven months.
Shoutout to Jeff Richards, James Alcorn, Ilir Sela, and Ben Christensen for helping brainstorm topics for Garrett.
Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get your $250 here.
Timestamps:
(3:44) More Gen Z than LinkedIn
(7:11) Helping frontier labs label AI data
(14:43) Masters and PhD students flock to Handshake
(16:52) Why Handshake will win in AI data labeling
(19:24) Growing to $250m+ Revenue
(21:56) KPIs in recruiting marketplace
(24:45) How AI will change careers
(33:57) How to build a Seal Team Six AI team
(37:06) Interning at Los Alamos
(40:00) Breaking into Silicon Valley from Michigan
(44:19) Helping friends get jobs at Palantir
(48:13) Driving across the US sleeping in McDonald’s parking lots
(54:52) Funding early days with his dad’s retirement account
(57:37) Handwriting letters to get the first six customers
(1:03:06) Early product failures and iterations
(1:11:01) Fundraising, crashing on couches for seven months
(1:17:07) Finally closing a Seed round
(1:20:05) Moving from Michigan to SF with no money
(1:23:38) Importance of sequencing new features
(1:29:10) Handshake’s exec recruiting process
(1:32:01) Building a company with your best friends
Referenced
Try Handshake
Careers at Handshake
Gumloop
Peter Thiel Startup School
Paul Graham’s blog
Follow Garrett
Twitter
LinkedIn
Follow Turner
Twitter
LinkedIn
Subscribe to my newsletter to get every episode + the transcript in your inbox every week.
The Expert Network Behind Handshake AI’s Model Training w/ Garrett Lord & Mamoon Hamid
Guests: Garrett Lord, co-founder and CEO of Handshake; and Mamoon Hamid, partner at Kleiner Perkins.
Handshake set out to democratize career opportunity. In the process, it unlocked something more: a high-trust expert network built on verified talent and earned trust.
This week on Grit, Garrett Lord shares how what began as a platform for student job seekers is now partnering with leading labs, enabling experts to train real-world AI systems. He explains how owning verified domain talent has become their core strategic edge, bypassing middlemen and turning a decade of trust into lasting advantage.
Connect with Garrett Lord
X
LinkedIn
Connect with Joubin
X
LinkedIn
Email
Connect with Mamoon
X
LinkedIn
Learn more about Kleiner Perkins
Co-Founder & CEO Handshake, Garrett Lord: The Billion-Dollar Question That Changed College Recruiting
Handshake CEO and co-founder Garrett Lord was amazed when he first learned that Silicon Valley firms like Google recruited on college campuses ... just not his, Michigan Technical University. But after excelling in the competitive Palantir internship program, he started asking himself, “How come they can’t reach us?” That question led him to found the job placement platform Handshake, which has raised $434 million in funding and is used by 100 percent of the Fortune 500.
In this episode, Garrett and Joubin discuss growing up in an “achievement-focused household”; how Garrett went from struggling to be noticed by Palantir’s recruiters to Handshake CEO; how his $1 billion-plus-valued company started with a broken-down Jeep; working without a safety net; why Garrett has changed his mind about hustle culture; “fortune favors the bold” and “no shave til you raise”; the relief of raising VC funding; how money condenses or extends time; and transitioning from scrappy to scaled CEO.
In this episode, we cover:
The impostor syndrome — and crucial epiphany — that Garrett had while interning at Palantir (05:46)
Starting the IT Oxygen club, and Trojan Horsing other college recruiters in Michigan (11:34)
Does having a chip on your shoulder make you more powerful? (17:08)
Living in the car, sleeping in McDonald’s parking lots, and showering at university pools (22:25)
Hard work and the importance of luck to Handshake’s success (27:08)
The difficult VC fundraising process, and finding a crucial ally: Former assistant dean of the Stanford GSB Andy Chan (30:55)
Handshake’s first office: A Palo Alto mansion owned by one of LinkedIn’s co-founders (37:55)
Growing fast and hiring a COO, Jonathan Stull (41:45)
Is Handshake the next LinkedIn? “Why not LinkedIn plus Indeed?” (47:16)
Links:
Connect with GarrettTwitter
LinkedIn
Email: garrett@joinhandshake.com
Connect with JoubinTwitter
LinkedIn
Email: grit@kleinerperkins.com
Learn more about Kleiner Perkins
This episode was edited by Eric Johnson from LightningPod.fm
.jpg?width=400){kind=small}
.jpg?width=400){kind=small}
